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Synthesis 1985; 1985(8): 749-751
DOI: 10.1055/s-1985-31331
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The Synthesis of Penicillanate Esters from Ultrasonically Formed Organozinc Intermediates

John Brennan* , Faiq H. S. Hussain
  • *Department of Chemistry, UMIST, P.O. Box 88, Manchester M60 1QD, U.K.
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Publication Date:
17 September 2002 (online)

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A series of 6α-bromopenicillanate esters 4 was synthesised by reaction of the parent acid with triethylamine and the appropriate alkyl halides in acetone. Reaction of these esters with zinc in dioxan with ultrasonic agitation led to the formation of organozinc intermediates for all of the bromoesters examined except the p-nitrobenzyl. Hydrolysis of the organozinc intermediates gave the corresponding penicillanate esters in 44%-72% yields.